Dibutyltin oxide → HCID 46831762, compound

HRID 530304Notes

Reaction equation

HRID 530304 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[CH:13][N:14]([C:16]([N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[O:17])[CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])#[N:2].C([Sn](CCCC)=O)CCC.[N:36]([Si](C)(C)C)=[N+:37]=[N-:38]>C1(C)C=CC=CC=1>[CH:20]1([N:18]([CH3:19])[C:16]([N:14]2[CH:15]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([C:1]4[N:36]=[N:37][NH:38][N:2]=4)[CH:4]=3)[N:12]=[CH:13]2)=[O:17])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 66681700HCID 66681700, compound

Product 1

HCID 46831762HCID 46831762, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(3-cyano-4-methoxyphenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide (305 mg, 0.901 mmol), dibutylstannanone (28.0 mg, 0.113 mmol) and azidotrimethylsilane (0.239 ml, 1.803 mmol) was heated in toluene (8 mL) at 115° C. for 20 h. The mixture was then cooled to room temperature and evaporated to dryness. The crude product was chromatographed over silica using a mixture of dichlormethane/methanol (95:5). After evaporation of the homogenous fractions, the residual product was triturated with diethyl ether, filtered and dried to give the product as off-white crystals, (196 mg, 54%).

Workup

  1. customevaporated to dryness
  2. customThe crude product was chromatographed over silica using
  3. additiona mixture of dichlormethane/methanol (95:5)
  4. customAfter evaporation of the homogenous fractions
  5. customthe residual product was triturated with diethyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-9b7c59838f884b568cd8a1b28bb514d2
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

Loading…